Fragile Lives, Shattered Dreams
by milomariano
Summary: Starting at Pilot Episode, Jess and Rory meet on her last day at stars hollow high. Rory also meets Logan, and the recent break up with Dean makes it incredibly awkward for them to be friends, so Rory isn't interested in a relationship. Can Logan or Jess change that?
1. Mind Astray

"I can't believe it's my last day at stars Hollow high! I'm totally going to miss this place," she said, kind of sadly, as she walked to the school in an over sized jumper and jeans alongside her best friend.

"Now my mother is going to have to find me a new protector from the dirty boys," Lane whined. "Not that you were such a great one..." she eyed Rory, thinking about the thing she had with Dean when they were 15.

"I swear to god, stop bringing that up. We're friends now, I don't want it to get awkward."

Lane scoffed. "Oh yeah, it's not awkward at all right now."

"Shut up!" She shoved Lane playfully, but she knew full well that her friend was right; things had been super awkward with Dean ever since they decided it was time to break it off, they had mutually lost their feelings for one another. No fight, or anything, just a sort of... what was the word? _Friendly_ breakup.

"Wow, speak of the devil, hey!" Lane greeted the beanstalk teenager looming in front of them, laughing as Rory was snatched from her thoughts and her attention brought to Dean. "Uh, hi. Dean."

"Hi."

"Hey."

"Okay, now we add another word, guys."

"Okay," Rory said. "Who's the new guy?" She pointed to a boy who seemed to be in their year, sitting on a bench reading a book – _Howl_ , she made out the title. He looked like a bit of a loner, but he looked nice all the same.

"I don't know, he looks rough," Lane mused. "But dreamy."

"Yeah. Dreamy. And he likes reading, that's always a plus."

Dean cleared his throat. "Guys, can we stop fawning over the new guy? He's staring."

Rory looked over to where he sat, an amused look playing over his lips. He smiled to himself, before looking back down at the book. "So, I'm gonna..." he gestured into the school building.

"Bye Deano!" Lane called after him.

"So, what do we do now?" Rory asked.

Lane smiled. "We talk to him, find out if he's really as rough as he looks."

Rory laughed softly. "I'm still waiting for the day when I can have your confidence, but okay let's go."

They walked over to the bench and stood in front of him. He didn't seem to notice them. "Watcha reading?" Lane asked, plopping herself roughly onto the bench next to him. When he didn't answer, she prodded him. "Helo-o? Earth to new kid!" Lane kept pestering him, while Rory just stood awkwardly to the side.

"What do you want? You selling cookies? Jeez," he scowled, returning to his book.

"Hey, we're just trying to be nice," Lane said, "Rory here likes that book, also."

Jess eyed her. "You read?"

Rory giggled, unsure as to why. "Uh, yeah, you can come see my collection if you like."

"Yeah, then we can have a slumber party!" Jess said sarcastically. "Look, I don't want to be an ass, but I'm already pissed off because I'm _here,_ and I don't want you to be on the tail end of that. So go away."

Lane gave him a questioning look. "And why are you –"

"Lane!" Rory dragged her friend away, leaving Jess in his own amused company.

As the bell rang, Rory and Lane made their way to meet Dean in their first class. As they took their seats next to the beanstalk, Lane started to chat to him, but Rory couldn't help but notice a familiar leather jacket-bound figure walking in the door, talking to the teacher with a smirk on his face. She almost laughed out loud, though, when the teacher made the boy stand in front of the class and introduce himself, his smirk turning to a scowl. "I'm Jess Mariano," he mumbled. "I'm new here, don't try to talk to me, I don't want to deal with anyone's rambling. I have so idea how long I'll be here for, so don't get used to my presence. There. Can I sit now?" The teacher nodded, and Jess took the only seat left in the class – the one on the other side of Rory.

"H-Hi," she stuttered. "Jess, right?" She never fumbled on her words, so why was she all of a sudden unable to grasp the English language?

"What did I say about not talking to me?" He frowned at her.

"Sorry. Forget I said anything."

"No... I just meant you obviously have a terrible memory."

"Why, thankyou."

Jess smirked, obviously amused by their ridiculous conversation. "So... who's the giant?" He gestured to Dean.

Rory went a little pink, saying,"He's, uh, my ex. But we're... _friends?_ I don't know what we are. We're trying to be friends, but it's really awkward."

Jess simply shook his head.

 _"What?"_ Rory asked, annoyed at how impossible he was.

"You can't be friends with an ex. Well, depending on how you broke up."

"I'm not telling you that!" She went a darker shade of red.

"I didn't ask you to."

"What?"

"I said, 'depending on how you broke up'. I didn't ask what happened, you got there on your own."

Rory frowned, her face fifty shades of purple. Why was she acting this way? She had only known this guy for... 40 minutes? Even when she had met Dean, she had a firmer grasp on speech... if 'the cakes are very round' counted as a good grasp. This was just normal... no, who was she kidding? There was something different about this guy. He liked to read – that was definitely something. He seemed to share her intellect, and (though she hated to admit it) the way he smirked... it was kind of... sexy?

"Rory? Care to answer the question?" the teacher was asking her a question, and she was too busy sorting out her messy head to realise it. She snapped out of her daze. "S-sorry. What was the question?" Jess snickered, earning a glare from Rory.

"What year did Shakespeare write _Othello_?"

Rory had a mental blank. She knew the answer, of course, but she was so messed up in the head that she couldn't think. After about 20 seconds, she stammered, "uhhhhh... 16-1604."

"Wow," Jess whispered. "You seemed like someone who would know the answer to that."

Rory turned fuchsia. "Shut up. I had a mental blank."

"What was distracting you?"

"Uhh..." she didn't exactly know how to phrase what she was thinking, but she was interrupted by the teacher.

"You two care to tell the class that private conversation you're having?"

"No, Miss." Rory sighed.

"Good."

As they got out of class, Jess tried to catch up with a jogging Rory, eventually falling in step with her. "Well, you really are a suck up."

"Thanks. Now go away."

"Actually, I think I might stay here," he mused. "What happened with you and Dean?"

Rory frowned, "What's it to you?"

"Well, you seemed very into _not_ sharing that particular information with me, so now I'm curious."

"Wow, this is coming from the guy who was telling me to stop talking to him this morning."

"Yep."

"I'll tell you Monday?"

"I heard rumours that you're not coming back on Monday. Something about a private school."

Rory rolled her eyes. "News travels fast. Even with your nose touching the pages of a Hemingway."

"Hey, in just an avid reader, like you."

"Yeah, but I don't read crap. Ayn Rand is _much_ more interesting."

"Ayn Rand is a political nut."

"But nobody could write a 40 page monologue the way she could."

"Whatever. I'm going to go back to my _Hemingway._ See you round... what's your name?"

"Rory. Well, Lorelai technically. My mothers name is Lorelai too. Weird, I know. She said that men name sons after themselves all the time, so why couldn't women do the –"

"Stop rambling, it's annoying."

Rory bit her lip. "Sorry. Bye Jess."

"Bye, Lorelai."

"It's Rory!"

"Sorry, Rory."

She walked off, a smile playing tenderly at her face. She had managed to actually talk to Jess, not just stutter out a few words. She was walking out of the building with a box of stuff when she crashed into a blonde guy in jeans and a grey shirt, the things in her box spilling everywhere. "Very graceful," he laughed.

"Wow, talking to new guys a lot today," she said under her breath, and the guy smirked.

"You think nobody can hear you, but your mumbling is incredibly loud, you know."

"No, I didn't know. Thanks. Now, either help me pick up my stuff or go watch a ball game, whatever." To her surprise, he bent down and picked up all her books and put them back into the box before she could even look down. "What's your name?" He asked, still picking up her stuff.

"Oh, it's Rory."

"Why, that sounds like one of my friends names. Never heard it on a female."

Rory blushed, for what felt like the 100th time that day. "It's actually Lorelai, Rory for short."

"Lorelai. That's a nice name. I'm going o call you that from now on." He got up, and smoothed his shirt. "Bye, Lorelai."

She stood still for a moment, before yelling, "wait!" He turned around.

"What?"

"You never told me your name."

"Oh, right. It's Logan. Logan Huntzberger."

Rory's eyes widened. "As in Mitchum..."

He scowled. "That's the one."

" _Woah_ , I've always wanted to be a journalist, and – and your dad, he –"

"Do you want to meet him?"

"I... wait, what?! Really?"

Logan smiled broadly. "Yeah, sure. Just so you know, he's kind of an ass."

"Sure he is," she said sarcastically.

Logan's face turned serious. "No, really. Obviously you can go meet him, if you _really_ want to... but he'll probably crush your journalism dreams. He'll tell you that you're not gonna make it. That you'd make a good secretary. Or someone who hands out sandwiches for the _Real_ journalists. But, as I said. Go ahead, meet him, whatever."

Rory cleared her throat. "Maybe I'll hold off..."

He smirked. "Good choice, Lorelai. See you round."


	2. Why are you dangerous?

**Chapter 2: You're dangerous because you don't know what you want**

"Mom! I'm home!" Rory kicked the door, knowing that if she let one hand off the box she was holding it would explode. "Mom!" She yelled. "Let me in!"

She heard Lorelai cursing. "Hold on, hon! Ouch!" She tripped over, causing a giant mannequin to fall on top of her.

Rory gave up trying to get her mom to let her in, instead slowly removing one hand of the box to twist the door knob. The sight she saw when she walked in was certainly unexpected, to say the least. Her mother was trying to disentangle herself from dark blue fabric, a mannequin pinning her legs down. Rory rushed over and pulled the mannequin off her mother. "Mom, what's this?"

"This," Lorelai gestured to the dress, "is your dress."

Rory had no idea what her mother was talking about, which happened often. "My dress for – uh – _what,_ exactly?"

"Ah," Lorelai smiled. "A little birdy called Emily told me that Bitty Charleston heard news of a big school formal which will be a month after you start Chilton!"

Rory was dumbfounded. "I am _not_ going to some ridiculous formal!"

"Why?"

"Because I have no date! Do you really expect me to bring some non-existent guy to a school dance! Also, I have no _guy_ friends to bribe into coming with me, so I'm going to turn up alone. Please tell me you didn't buy tickets online?!"

Lorelai blushed. "I did."

"Oh my god, mom! You didn't even bother asking my opinion?"

"I knew you'd say no..."

"And you have to respect that! Now everyone will know I bought tickets so I have to go!"

"Well, you could always pretend you're sick?"

Rory sighed. "Yeah, I'll come down with that rare flu that only hits losers on dance night!"

 _" Rory,"_ Lorelai scolded. "You're not a loser! Just go alone!"

"No way," Rory said. "I'll find a guy, I guess."

"That's my girl," Lorelai ruffled Rory's hair before watching her daughter disappear into her room.

* * *

"Lane!" Rory called up the stairs after Ms Kim let her in the house.

"Rory?" Lane called down the stairs as she emerged from her room. "What are you doing here?"

Rory ran upstairs into Lane's room and shut the door. "I don't have a date!"

"You... what do you mean?"

Rory sighed. "Mom bought tickets for this school dance that's on a month after I start Chilton. And I don't have a date!"

"Oh, god. She should have asked you, right?"

"Yes. She should have, but now I need a date!"

Lane reddened. "You could... you could always ask Dean?"

Rory's eyes widened, "What?!"

"I mean... I know he's your ex, and all. But really, what can you do?"

"You're crazy," Rory muttered, running out of the house.

"Mom!"

"Rory?"

"I think I've found a date!"

Lorelai hugged her. "That's great, hon! Who?"

Rory shrugged. "Oh, um... Dean."

Her mothers eyes widened. "Dean... Dean – Dean Forester?!"

"It's my only option!"

"And you're sure he's up for this?"

Rory blushed, "Well, I haven't exactly asked him yet..."

"Oh, hon. You have to ask!"

"I will. I mean, I know I'm not with him anymore, but we're always trying to be closer friends, and what better opportunity than this, right."

"Rory. This is _so_ out of line! You can't just use your old boyfriend so you won't look like a loser!"

"I'm not!"

"You are! You are, Rory!"

Rory started to pout. "I don't need your permission anyway, I'm doing this. _You're_ the one who bought those stupid tickets in the first place!"

"Rory..."

"I'm going to go ask him."

"Rory-"

"Bye!" She ran out of the house and down the street to Dean's house on Peach.

"Dean?" Rory knocked on the door. "Dean, you home?"

She heard footsteps coming to the door and Dean appeared. "Hi Rory... what - what are you doing here?"

"I have to ask you a favour..."

"Go ahead," he shrugged.

"There's a formal at Chilton, it's a month after I start, and I... I need a date."

"Oh..." Dean froze.

"I thought, since we're trying to be friends again, we should do things together. We don't even have to dance!"

"Wouldn't it be weird, though?"

"It won't be weird. I don't know anyone, and I probably won't know anyone of use in a month, nobody will know who you are. We'll go, we'll eat, we'll leave. That's all!"

"Uh...no."

"Please? I'm begging you!" Dean looked away, and Rory turned his head so he would look at her. "Say something," she said.

"I'm sorry, Rory. I can't do that. I can't... take you to something that you're supposed to take your boyfriend to."

"You're sure?"

"Yeah... I'm sure."

"Okay, well... sorry for bothering you. Bye Dean." She walked out the door and down the street, avoiding Deans gaze. He knew she meant well, but he knew this dance would only bring up memories of the past, when they were together. He didn't love her anymore, of course, but part of him still knew that he was at his happiest when he was with her, and he didn't want to be so happy in a moment with Rory that he would do something stupid. So he had to say no. For her sake.

 **The next Monday:**

"So how many dinners do we have to go to before we're done paying Grandma and Grandpa back?" Rory asked as mother and daughter had an early breakfast at Luke's.

"I think the Friday before I die will be the last one." Lorelai said snarkily.

"Don't be stroppy about it, there's nothing we can do," Rory replied.

A voice sounded behind her, a hand coming out of nowhere and refilling the Gilmore Girls' mugs of coffee. "Nothing you can do about what?"

The voice sounded familiar. Almost like... "Jess?" Rory asked, turning around, getting an eye-full of Jess smirk. _Not necessarily a bad thing,_ she thought. _Wow, weird thought, Rory._

"Yep, that's my name. And you must be Rory, the private school girl. I like the uniform. It looks like you've been swallowed by a kilt."

Lorelai smiled. "That's what I said!"

Jess smirked and gestured to Lorelai. "So, this your mom?" He asked. "The famous Lorelai?"

" _Famous?"_ Lorelai raised an eyebrow. "Rory, do you know this guy?"

Rory went pink, but she didn't know it. "No. Well, he went to Stars Hollow High, so I've seen him. But- but I go to Chilton now."

"Thanks for the update," Jess and Lorelai said in unison.

"You're welcome," Rory awkwardly said, eliciting a smirk from Jess and a smile from Lorelai.

Lorelai went pink. " _I'm_ supposed to say that 'thanks for the update' thing, Jess. She's _my_ daughter, why would you know she's going to Chilton anyhow?"

Rory frowned and shook her head vigourously while trying to remain unseen, much to Lorelai's amusement. "Trying to hide something, hon?"

"No, mom. This is Jess, he started at Stars Hollow High last Friday."

Lorelai raised an eyebrow. "And how did you meet him?" She asked, as Jess smirked.

Rory opened her mouth to speak, but Jess cut in. "As I walked in the gate, she was staring at me. So I smiled at her, and I took out a book. Then she started grinning ear to ear because she likes reading too, right? Anyway, then she came up to me and started babbling about how Hemingway is boring-"

"Right on," Lorelai laughed, winking at Rory. She waved for Jess to continue.

"And then we started talking. That's it."

"You really need to work on making your stories a little more interesting... Jess, was it?"

"That's me."

"Great. Could you leave us alone for a minute?"

"Sure," he smiled and left.

"Rory, is what he said true? That you approached him?" Lorelai raised her eyebrows over her mug of coffee.

"Ye-no," she admitted. "Lane saw him reading and didn't recognise him, we asked Dean who he was and he told us that Jess was new, Lane dragged me over and make me talk to him. That's all."

Lorelai looked Rory in the eye. "I think he likes you, babe."

"Mom!"

"The way he was looking at you, the way he smiled. He doesn't seem like the kind of guy to smile much."

"He smiles a fair amount."

"When you're looking."

Rory frowned. "Well, I don't exactly see what happens when I'm _not_ looking!"

"Fair enough, but when you guys are 'looking' at each other he's very smiley. _Very_ smiley." As if on cue, Jess smiled and waved in Rory's direction, before noticing Lorelai staring and going back to pouring his coffee. "He likes you."

Rory looked down at her coffee. "He's kind of acting the way Dean acted when I met him."

"Which is how?"

Rory got a faraway look in her eyes. "Well he's always intentional about being nice to the people who he knew meant a lot to me, and judging by the way he's talking to Kirk right now – jeez! – he's not normally that tolerant with people, but he made an effort with you. He's nice, and he makes jokes about my lifestyle, just a bit. I don't know, it's just... Dean..."

"Honey, I know you're still in shock over Dean. But let's just look at the Jess issue: do you think he likes you?"

Rory started to rise from her chair, getting her bag on her back to go to school. "I don't know. We'll have to find out, won't we? We have to get to school."

"Right behind you, hon." Lorelai walked up to the counter to pay, and Jess was there. "Hey, can I talk to Luke?"

Jess frowned. "He's busy. I'm here, do you want to pay?"

Lorelai pouted. "I know you're there hon, and I'm happy you are, because whatever you are to Luke, he'll tell you lies about me."

"Do you want to know what I am to Luke? Why I'm here? Why I'm working here?"

"That was what I was going to ask him, but it's great coming from you too."

Jess smirked, that smirk that Lorelai had already seen Rory react to. Rory liked that smirk. "I'm not in trouble or anything. I'm not a criminal."

"That's... great." Lorelai said awkwardly.

"My dad recently left my mom and I, and we had no money. She's a crackhead, Liz, and any money that she _did_ make went to gambling and buying drugs. She never had time for a kid."

Lorelai put her hand over Jess', but he pulled away. "That sounds horrible, a kid shouldn't have to deal with that."

"Well, it's done. What can we do now, right?" He shrugged. "Anyway, so Lizzy made us move into Beenie Morrison's old place. Just down the street from that crazy woman Babette's-"

"And very close to our place."

"And Luke's my uncle-"

Lorelai spat her coffee all over Jess. "He's your WHAT?!"

"My uncle," Jess laughed. "My mothers brother."

"Oh, my god. Continue."

"So I'm working at the diner to earn some extra cash, Liz won't work she just sits with her feet in a bowl of hot water all day."

"Wow, no offence but your mom seems horrible. And you seem like a nice kid, Jess. I'm really sorry."

"Thanks, Lorelai. I've gotta go pour some coffee for Miss Patty over there-"

"Be careful with her," Lorelai joked, Jess nodding as he walked away. Lorelai had no idea that Luke saw the entire exchange between her and Jess, and he was thrilled that Jess and Lorelai were hitting it off – it could even give Jess a shot with Rory.

"Jess!" Luke pulled him away from Miss Patty, leaving the coffee pot discarded on the table. He pushed him into the storage room. "I have to talk to you."

"Great," Jess grimaced, feeling as if he knew what was coming. The talk. About Lorelai Gilmore's very attractive daughter who was in his year, and who he was only slightly into, Luke would be saying that she's the one girl in town that's off limits. Seems to work out that way normally, doesn't it? Besides, she was talking to a certain Huntzberger boy on Friday who Jess could very well assume was now Rory's boyfriend. "What do you want to talk about?"

"Not a what," Luke stated. "A who. A certain..." Jess waited for Luke to say a name. "Rory Gilmore."

Great. Just great.


End file.
